


Brooklyn 99 headcanons

by raggedy_ginger



Series: Headcanons [1]
Category: Brooklyn Nine-Nine (TV)
Genre: F/F, F/M, Gen, Headcanon, M/M, Multi, Poly and monogamous headcanons, Polyamory, Slice of Life, Why yes I'm thirsty for them all, fight me
Language: English
Status: In-Progress
Published: 2020-01-14
Updated: 2020-01-14
Packaged: 2021-02-27 14:47:03
Rating: General Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 6,829
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22258927
Author URL: https://archiveofourown.org/users/raggedy_ginger/pseuds/raggedy_ginger
Summary: Headcanons about what it would be like to date some of the 99 squad.Requests are open!
Relationships: Amy Santiago/Reader, Jake Peralta/Amy Santiago, Jake Peralta/Reader, Kevin Cozner/Ray Holt, Kevin Cozner/Reader, Ray Holt/Reader, Rosa Diaz (Brooklyn Nine-Nine)/Reader
Series: Headcanons [1]
Series URL: https://archiveofourown.org/series/1712944
Comments: 2
Kudos: 63





	1. How you meet

**Author's Note:**

> Hello, yes, another project I'm starting because I'm weak and this makes me happy.  
> Basically each chapter is a short headcanon for each character based on the topic.  
> Feel free to suggest anything you want to see!

Jake  
Your precinct absolutely obliterated the 99th during one of the tactical bootcamps. Getting to see the arrogant Jake Peralta with that aghast expression and paint splattered all over his vest after you'd shot him and officially won the game was the highlight of your year.  
Afterwards, while rounding up your people and gear the detective made his way over and loitered around a crate of surveillance gear.  
"Peralta," you said with an expectant eyebrow raised.  
"Detective-"  
"Sergeant now actually," you corrected smugly.  
"Congrats!" He said sincerely and you bumped the fist he held out without hesitation.  
"Thanks dude, was a good game out there. You guys almost gave us a challenge." There was a teasing grin that the other man returned.  
"I dunno, I think it was a once off." He had an upward swing to his voice that suggested he had a plan to this banter.  
"What are you suggesting?"  
"Rematch," there was that shit eating grin of his "Lazer tag."  
"You're on."

-  
Amy  
Being a graffiti artist was a double edged sword. On one hand it was way more exhilarating than any of the gallery work you'd ever done and the community of painters that decorated the streets of New York was pretty tight.  
On the other hand if you got caught by any authorities it kinda bit you in the ass.  
Luckily the cop that caught you spraying the walls of a backstreet happened to be extremely cute, and extremely law abiding.  
That part was a bummer. 

She hauled you back to her station and got to work filing up a report and various fines. When she asked for your name and you distractedly gave it to her because damn that bald man a few desks away had just bitten off half a sub and swallowed it like it was nothing. Detective Santiago -she had introduced herself when she was cuffing you- had let out a small gasp.  
"But you're my favourite modern artist! What-why were you?" She ended that articulate sentence with an outraged splutter.  
At this you leaned forward and abandoned your observations of the bald man aggressively attacking a hamburger now.  
"Art doesn't belong in a frame, Detective Santiago, take yourself as an example." The subdued squeal that escaped her throat without her mouth really opening made the whole thing worth it.

When the paperwork was finally finished and you were mostly free to go you made sure to mention quite loudly to no one in particular that the newly repainted walls about a block from this precinct were looking rather bare still. Santiago definitely made a note.  
A literal note. 

-  
Rosa  
The lady in leather dropped by your flower shop an awful lot for someone who didn't buy flowers.  
At first when she started coming in, browsing for a minute and then leaving you had worried that maybe your stock wasn't enough.  
But then you'd noticed how half the time she wasn't looking at the flowers and the other half of the time she was smelling the fake plastic flowers. What really tipped you off was that sometimes her friends would wait outside, and if you were close enough to the door when watering plants you could hear them talking about the leather lady's newest crush who just so happened to be a florist. 

And one does not simply let an opportunity to shoot your shot pass.  
So you made a guess, wrote a note and waited for her to drop by again. 

You were lucky the shop was empty when she came again. You grabbed the bundle of flowers and tucked the note in between the ribbon tied strings before shoving them at her without preamble.  
"Ah, sunflowers and my number." You announced awkwardly.  
"Uh..."  
"Sunflowers because you brighten up my day and my number because if you wanna get to know me I'd like that alot."  
She was frowning, glowering even but she took the flowers quite delicately.  
"Cool." She grunted and promptly left.

-  
Holt  
The FBI could call it what they wanted; informant, red herring, whatever. You were a snitch, and you knew that.  
It wasn't great, you were constantly looking over your shoulder everywhere you went and you didn't trust cops, criminals or citizens because you had a lick of sense or maybe a sense of paranoia. 

And that lick of paranoia was proven right when two cops appeared out of nowhere in the middle of a chat to one of your neighbours and slapped some handcuffs on you before dragging you to the 99th precinct.  
"You didn't even read me my full rights!" You pulled and wriggled in their grip as they herded you into an interrogation room with some snarky commentary that you was too scared to pay attention to. The two of them left you in the uncomfortable plastic chair and left the room.  
You shifted in your seat and tried to settle down, you needed to calm down. This could be a dirty cop situation sure, but it could also be law enforcement getting in touch with you for information. It would be great if they could just send a muffin basket with a card instead but no. 

It wasn't long before the door opened again and a stoic man stepped into the room. A captain, you noted while inspecting his uniform and maybe how well he wore it.   
"I am Captain Holt of the 99th precinct." He introduced himself as he took a seat across from you.  
"You're the one I've heard so much about then." You mused mostly to yourself but the Captain's brows furrowed minutely for a second before his blank expression returned.  
"I need some information."  
"And I need some coffee."  
"Don't we all," He deadpanned and you cracked your first smile that morning. 

-  
Kevin  
It was the dog. That damned dog. 

You were sitting on a park bench reading when a dog that looked like a stack of hash browns came barrelling towards you and took a flying leap into your lap. The mud on his paws smeared all over the pages of your book and you couldn't help but let out an annoyed growl that was followed by an actual growl. It just wasn't a growl from you.  
An overly excited Labrador bounded towards you, eyes intent on the shivering corgi burrowing into your jacket.  
You stood, tucking the small dog under your arm and squaring your shoulders before letting out a sharp hissing sound at the lab that seemed to snap him out of his excitement.  
"Sit," you commanded in a firm voice that was followed by the full thud of a compliant dog. You reached for the dirt covered leash attached to the bigger dogs harness and with your ruined book in your pocket you set off towards the sound of names being yelled.  
It was easy enough to find the owners of the missing pets. They were yelling heatedly at each other in between shouts of , "Cheddar," and "Sam". Both men ceased their shouting when you emerged from the thicket of trees with both dogs.  
You handed off the lab to the man that rushed forward to gush over the dog and strode over to the still glaring man in the sweater.  
"Your dog ruined my book," you said as a greeting while reluctantly handing over the admittedly adorable corgi. When your hands were free you waved your copy of The Odyssey around, showing off the small pawprints decorating the otherwise plain cover.  
The mans glare softened when his dog was safely in his arms, and melted even further into curiosity at the sight of your book.  
"You enjoy Greek mythology?" His voice was actually quite pleasant when he wasn't yelling Cheddar.  
"Immensely. Although I don't think Cheddar here appreciates the finer points of literature." You directed a pointed stare at the dog as he happily panted in his master's arms.  
Lucky bastard, you thought quietly.  
The man let out something that could be considered a chuckle. "I am Professor Kevin Cozner. And no, Cheddar does not appreciate the classics."  
"Well, he's much cuter than the other dog so it's okay." You replied with a warm smile. And so is his owner, you added silently.


	2. How a date occurs

**Summary for the Chapter:**

> How a date arises

**Notes for the Chapter:**

> I'm planning to do Poly headcanons for Jake/Reader/Amy and Holt/Reader/Kevin that will stem from one of the characters either of the pair has become involved with.   
> So like for Amy and Jake the artist will probably be the character they both date in the end. 
> 
> Let me know what you'd like to see!

Jake   
He never seems to realise that his white sneakers always give him away in the UV lit Lazer tag arena. At this point it definitely feels like cheating to destroy him once more.   
But you shoot anyway and the game is over with much grumbling from the detective and much crowing on your part.   
It's only later that evening, when the two of you are eating pizza and chugging down sugary sodas in the restaurant above the arcade that you find the courage to bring up the subject. 

"Do you think that maybe Lazer tag is getting a bit old now?" You said carefully while taking a well timed bite of pizza.   
"Whaddya mean?" Jake asked around his own mouthful of pizza.   
"I mean I love annihilating you but maybe we could do something else for once. Like I could... Take you out somewhere nice?" Wow, real smooth.   
His eyes narrowed at you before he swallowed and only just avoided choking.   
"Like a date?"   
"No no," You interrupted and his shoulders did that depressing slumping thing "Not like a date. As a date."   
It took him a second but that brilliant smile was worth every overpriced dollar you'd spent on laser tag. 

-  
Amy  
Out of anyone Amy would appreciate a good pamphlet. In fact you had heard her mention a pamphlet collection with a sense of pride in her voice.   
So you thought that she'd appreciate the enveloped pamphlet and ticket to your gallery opening tucked into your back pocket when you planned to be arrested for some open air artwork. 

Except that she wasn't on shift, and a much harder looking cop had arrested you with far more force than Santiago usually did. The handcuffs were biting into your wrists almost as you were walked through the station with the leather lady prodding your back every now and then as you took too long while looking for your detective.   
"Uh, is Detective Santiago okay?" You tried to ask casually but the woman just gave you a hard stare as an answer.   
"She's usually the one who writes me up and I just..." You continued valiantly before realising you sounded like a complete lunatic.   
Maybe it hadn't been such a great idea to invite the detective to your new collection. Just because you had gotten to talking and some flirting whenever you ran into each other didn't mean she was interested. She did kind of view you as a criminal after all. And the repeated offended were piling up.   
Maybe it was time to stop? 

You sighed and slouched back in your chair, resigned to giving up your pursuit for Santiago's affections when the woman herself marched out of the elevator and did a double take when she saw you at her colleagues desk.   
She did that funny shuffle run over to you and cleared her throat awkwardly.  
"Hey Rosa, I don't mind taking over for you if you want to take a break." There really was nothing casual about the way she asked despite her obvious attempts to make it seem like it was.   
Rosa's eyes flitted between the two of you before she smirked.   
"So you're the artist." Rosa said in a successfully casual way and left the two of you alone.   
Santiago took her seat and seemed almost nervous now that you were alone. 

"Hey, Detective. Your colleague didn't make sure that that envelope wasn't laced with crack or something." You waved your handcuffed hands a little at the envelope on top of your belongings as Santiago have you an incredulous stare.   
"I'm pretty sure Rosa would-"  
"It's for you." You interrupted and hoped that for once she'd go along with your cajoling.   
She gave you a suspicious stare but reached for the envelope and opened it anyway. 

She handled the glossy pamphlet with great care and the invitation with even greater attention.   
"I'd like to try and get to know you outside of these handcuffs." You explained with a nervous smile.  
Her fingers lingered over the images of your art before she looked up with the softest smile you'd seen from her.   
"I'd like that." 

-  
Rosa  
She's pretty straight to the point. Which is ironic because was actually bisexual.   
That was one of the jokes you liked to annoy her with when she started texting you. 

It was only a few weeks after you'd given her your number that she'd sent you a minimalist text.   
(You busy tonight?) She messaged.   
[Nah, you?]   
(Yeah, going on a date with you. See you at 6) 

And that was that. 

-  
Holt  
There was just no way you'd ever be acting on your growing feelings for the Captain, let alone ask him on a date. And that was only partly due to the wedding ring on his finger.

Your interactions were mostly limited to the times you were dragged into his precinct and placed in the interrogation room, although over time the chairs got more and more comfortable and there was always a coffee waiting for you.   
It was probably the best relationship you'd ever had with law enforcement. 

Then came the day that you'd signalled one of the 99 detectives, Diaz, to arrest you ASAP. She'd given a curt nod and had tailed you into a back alley where you'd held out your wrists expectantly with a clear bag of giggle pig in your hand. She'd said nothing as your hands shook when she'd cuffed them and confiscated the drugs.   
You got to the station without a fuss and she'd taken you to the usual room and left you alone.   
You'd let yourself slump in your chair and clenched your hands tightly to try and calm the tremors.   
Your head was resting on your joined hands when the door opened and familiar footsteps filled the room.   
You looked up to see Holt with a mug in one hand.   
"Ah, so you're the one who's been making coffee all this time." You greeted weakly as he handed you the mug and you wrapped your hands around the warmth.   
"Why are you here, your cover could be compromised by you signalling-"   
"My covers already blown." You blurted out. "I found one of the giggle pig sources and they wanted me to take some to show loyalty or some shit." 

There was a sharp intake of breath from Holt and a soft oh.   
"But they must have known, someone knew I was a snitch and snitched on me." You laughed bitterly and hunched in further on yourself. "They trashed my apartment, took everything while I was out high as a fucking kite because they made me take their shit. Fucking hell, they were gonna fucking kill me." You let out a shuddering breath and lowered your shaking hands to the table so you wouldn't spill coffee.   
"I don't have anywhere else to go, Holt. If I leave this station, if I go back home they'll kill me or worse-"   
Heavy hands on my shoulders stopped your panicked rambling that was veering into hyperventilating. 

"You're not leaving. We're going to keep you safe." He was staring right at you with those dark eyes. Deadly serious even more so than usual. "I give you my word." 

Holt was the only thing keeping you from being murdered out on the streets. There were no words for that kind thing.   
Were you supposed to say something about your growing admiration for the older man? Admit that maybe your admiration was more than that?   
No fucking way was that happening. You would do what all sensible people did. You would feel all your feelings, keep them in your chest until one day - you would die. 

-  
Kevin  
Seeing Cheddar bound towards your usual seat had become your favourite part of the afternoon. Because it meant that shortly after Kevin would round the path, strolling formally towards you like it was happenstance that brought him here most days.   
You looked up from your book and smiled at the man.   
"Ah Professor," you said warmly as Cheddar nudged your leg for attention and you happily scratched his ears.   
"You shouldn't indulge such behaviour." He scolded as usual and sat next to you.   
"I'm a sucker for the little guy." You set your book on the bench and patted your lap so that the little dog knew it was okay to jump up. 

Luckily the cold winter had remained dry so far and so his fluffy paws were clean.   
You buried your cold hands in Cheddar's thick fur, feeling silly for once again forgetting gloves and envious as you looked at Kevin's soft leather gloves.   
In fact you felt a bit more than envious. There was just something about how the leather clung to his hands, showed every flex and tensing of the muscles. It was rather distracting to be honest. 

"What are you reading today?" He asked while watching you fawn over his dog.   
"Oh," you picked up your book and handed it to him "You spoke about it last week. And there's no better way to get to know someone than reading the books they like."  
His ran his thumb over the spine and directed a disappointed look at you.  
"You cracked the spine," Kevin's usually tempered voice was slightly outraged at this.   
"It's a sign of a good book!" You protested and refused to give out against his raised eyebrow.   
"It's a sign of a careless reader." He shot back.  
"Interest!"   
"Distraction." 

You pursed your lips and politely snatched your book back.   
"We're different breeds of literature lovers I'm afraid." You tried to broker. He hummed in response.   
"Except that I have a degree in the field, which makes me the current authority between the two of us." You narrowed your eyes, because you knew if this was anyone but Kevin they'd be wearing a shit eating grin.   
"Then I shall relinquish custody of this book to you." You passed the book back to him after sneakily slipping a slip of paper between the pages. "And I shall bid you farewell."   
With one last pat for Cheddar you stood up after he hopped off and held out your hand to Kevin. 

He looked at it for a moment before reaching out and clasping it with his own. This was the first physical contact you'd had with the man since meeting him a month ago.   
It was just a cordial handshake, one firm shake before you withdrew.   
"I'll see you soon, Professor." 

You walked away, not turning around to see if he had opened the book yet to find the handwritten note with you expressing a desire to see him more often along with your number.   
But when you came home from work a few days later and saw a text from an unknown number you knew no one else would text so formally. 

(I have enjoyed our time spent together in the park and would not be opposed to getting to know you further.   
If you are in agreement I shall arrange for a dinner at a local restaurant on Tuesday next week. 

Please get back to me when you receive this message. 

Regards,  
Professor Kevin Cozner.) 

Plus he signed it.


	3. The first date (or something resembling it)

**Summary for the Chapter:**

> How the first date goes!

Jake   
You weren't sure why Jake was wearing a short sleeve shirt and board shorts at 7 in the evening.   
If it had been anyone else you would not have laughed so hard.   
"Taking casual Friday a bit too far, Jake." You teased as you walked the sidewalk together.   
"A dude barfed all over me when I was leaving and I didn't wanna be late, so the the only choice was clothes I collected from the 99's lockers." He griped and rubbed his arms to try and ward off the cold.   
"Where are we going anyway?"   
"There's a fair type thing a half block from here, I thought it would be fun to expand our competition to things other than laser tag."   
"Cool. Cool. Cool. Cool."

The detective liked to goof off alot but he always came through when it mattered, and it warmed your heart to see this dork in his awful pineapple slut shirt and Hawaiian themed shorts.   
It wasn't a hard choice when it came to slipping off your jacket and holding it out to your shivering companion.  
"Nah, it's-"   
"I wouldn't want my date freezing before I beat him at ski ball." You interrupted and bumped your shoulder against his.   
Being cold was worth seeing him in your coat. 

He did beat you at ski ball but he looked remarkably cute while doing it and you crushed him later at shooting bottles, so it was okay.   
The night wore on and the two of you worked your way through the whole fair several times until the stalls started closing up and you were one of the last few people left walking.   
You had lost track of time, it didn't matter that much when his hand was intertwined with yours and you kept nudging each other to see who would fall. 

"Hey Peralta."  
"Yerp?"   
"Can I kiss you?"   
He had the smarmiest grin ever, and you took great pleasure in making it disappear when he nodded and you leaned in to kiss his dumb face. 

-  
Amy   
The gallery was quietly loud in the way that only galleries and busy bookshops could be.   
The low murmuring of people talking and some classical music playing in the background helped to soothe your nerves as you smiled and chatted with patrons of the gallery about your new exhibit while scanning the room for any sign of Santiago. 

In the end her entrance couldn't be missed.   
The doors were pushed open with an echoing bang and she hurtled into the room, still in uniform and with a bulletproof vest on as a bonus. That certainly cleared her path, although she wasn't quite sure where she was going.   
You quickly excused yourself from current conversation and waved at the detective through the crowd.   
"Santiago!" You greeted far too loudly for her comfort as you made your way to her. "I know our first meeting was you arresting me but I guarantee you I'm not going to escalate my crimes further."   
She rolled her eyes and let you guide her by the elbow.   
"We got a tip off and had to act tonight, that's why I'm late and-" she gestured at her attire.   
"You look dope as fuck, Santiago." The uniform had an effect on you, not saying what effect but there was one.   
And it seemed that your own clothing was having an effect on her too judging by the way she kept staring you up and down with an incredulous expression. 

She'd never seen you out of your painting clothes, so seeing you in your fancy formal wear was definitely different.   
"Uh yeah, you look... Good too." You shot her a grin, the same one that you wore when she wrote up your paperwork and that seemed to settle her nerves.  
"So art or the real work of art?"   
"Real work of art?"   
"The buffet." You replied cheerfully and she huffed.   
"Art first."   
"As the lady commands." You gave a mocking bow and she smacked your arm. 

You'd heard about how it was easy to fall for someone when you watched them doing something they loved. And watching Amy over analyse artwork and fawn over her favourite artists you finally understood why.   
She was so passionate and unashamed of how nerdy she was. It was glorious. 

There was a warm full feeling in your chest that was only partly due to too many tiny sausage rolls from the buffet.   
"Amy," you murmured softly and stepped close enough for your hands to brush as she admired one of the paintings.   
"Finally dropping the detective." She smirked.   
"Well we're not together in a professional capacity right now."   
"Why do you say right now?" She narrowed her eyes at you and you hummed.   
"I had a great idea for a new mural. Hey, ow!" You rubbed your arm from where she punched you.   
"I can't keep arresting someone I'm entangled with, it's unethical."   
"Oooooh, we're entangled are we." You teased with a delighted grin. "Ow!"   
She punched you again but this time cut off your complaining by pulling you in for a kiss. 

Short, sweet, and with more teeth than you expected.   
Much like her really. 

-  
Rosa   
She does pick you up at 6 as promised. You go to a restaurant you'd never known existed and when asked she'd said something about a food obsessed work friend and you'd decided not to ask further because to be honest you were afraid she'd just shut you down and you weren't sure how well you'd handle it.   
So instead you kept the conversation light, talking about nothing in particular until you saw an old classmate from high school and lost all sense of decorum. 

"Do you ever just see someone and feel a deep sense of rage ignite in your bones." You half asked while watching that annoying person who'd always set off your temper walk by the window.   
"Yes." Rosa answered evenly while swizzling her cocktail.   
"Did you have something planned tonight?" Seeing your old schoolmate had fired up something restless in you.   
"Nope, why?"   
"Come on." You slapped some bills on the table to cover your tab and grabbed Rosa's hand to pull her out of the restaurant and onto the sidewalk. "I want you to remember this night for the rest of your life, Rosa Diaz. And that won't happen if we're sitting in that restaurant making meaningless small talk. I'd rather not talk if what I say is a waste of words." 

"So," you squeezed her hand "do you want to wreak havoc with me tonight?"   
Her slow smile and the tightening of her hand around yours was the only answer you needed. 

-  
Holt   
Safehouses were very boring.   
No internet, no visitors and no leaving. Around twice a day a cop would drop by to replenish your supplies and do a perimeter sweep. If you were lucky they'd deem you worthy enough to talk to. And if you were really lucky you'd get one of Holt's detectives, who'd always spend an extra few minutes treating you like a human being.   
But even with that you were wearing thin. Being alone and constantly afraid for the past few weeks had taken its toll. You were tired and anxious all the time, sleep didn't come often enough and even food was beginning to lose its appeal. You were losing hope that you'd ever leave this safehouse alive. 

You were sitting on the floor, out of sight of the windows, and moving food around on your plate when Detective Peralta let himself in. You tensed and reached for the knife you'd stashed in the makeshift sheath strapped to your ankle.   
"Heyo!" He announced as he casually dropped to four legs and crawled on over to you.   
"Hey Jake." You greeted quietly.   
"How's the binge watching going?" He nodded to the TV where a David Attenborough series was still playing.   
You shrugged, "It's alright."   
He watched you push your peas around, seeming to take note of more than your lackluster replies.   
"So uh, how are you holding up?"   
You paused in your peas pushing and then shrugged again.   
"I'm alive."   
That was not what he wanted to hear. He frowned and made loud thinking noises before leaving your side and crawling back to the door.   
"I'll be back in a minute." He called across the room before closing the door and leaving you alone. Again. 

It was far longer than a minute. You were lying down on the carpeted floor and half watching the documentary when there was a firm knock on the door before it opened.   
"Attenborough is talking about penguins again, you like penguins right?"   
"I have no strong opinions on the species." Came the Captain's voice instead of Jake's. You twisted your head around to look at him as he got on all fours and somehow shuffled to you while retaining his dignity. 

"Holt." You said stupidly as he sat next to you, leaning his back against the couch.   
"As I am not here in a professional capacity I will allow the dropping of titles."   
"Very generous of you." You commented dryly. "Do you want something to eat or drink?"   
"I ate before Peralta called me."   
"Ah."   
You weren't going to probe further, or ask why he had come. Never look a gift Holt in the mouth. 

"Wanna play chess while we watch penguins fight for survival?"   
"That sounds like my Saturday night." He deadpanned and you took that as a positive and hauled out the chessboard you kept amidst the stack of books and DVDs.   
"Get ready to be annihilated, Holt."   
"I believe it is you," he tilted his head challengingly "who should be ready for annihilation." 

Turns out you were absolute trash at chess as soon as your opponent was someone who knew how to play.   
Holt sat across from you, resting his chin on his hand and watching you as you deliberated over your next move.   
"So why did you come? I'm assuming Jake called you after your dinner and you're married and all..." You asked while moving your Knight in a way that made something in his face change. You cursed silently.  
"During actually." He corrected and brutally murdered your Queen in one move.   
You cursed out loud but the sacrifice felt worth it when the man actually smiled.   
"And I came because Peralta said you needed a friend." 

That did throw you off, although you considered him a friend you weren't sure the feeling had been reciprocated.   
"I did. I'm grateful you came." You moved your innocuous pawn and knocked over Holt's king with a satisfying click. "I wouldn't have been able to beat you if you hadn't."   
You grinned proudly at seeing the other man narrow his eyes at the board as he analysed the strategy you'd barely managed to pull off.   
He looked up at you with an impressed raised of his brows.  
"Very well done." His voice did not send shivers down your spine. 

You'd never felt so motivated to get better at chess before.

-  
Kevin  
The restaurant was intimidating.   
And you thought you'd gotten over Kevin being intimidating but now he was in a suit in a fancy restaurant and it was intimidating.   
You felt underdressed in your white collared shirt and tie. He'd told you it was fancy and you'd thought you'd dressed appropriately but people here looked like they were on their way to the opera. 

Kevin definitely did not seem impressed with your attire, his gaze lingered on the crease in your shirt and the slight looseness of your tie and his eyes narrowed just that little bit.   
"Hey," you greeted him warmly despite feeling like you should have stayed at home with a good book.  
"Good evening," he drawled in a controlled tone that felt cold rather than restrained. 

He rose from his seat to greet you with the usual handshake before the two of you sat down.   
"Sorry about my clothes, I didn't know we'd be going somewhere so..." He raised an eyebrow at you. "Upmarket."  
"It's alright. I should have been clearer in my message." His face softened almost imperceptibly.   
"It's a bit odd seeing you without Cheddar." You commented to move the evening along as you glanced over the menu.   
"I must admit, it is is odd seeing you without a book."   
"Who says I haven't got one in my back pocket?"   
He let out a huff of laughter as he looked up at you. "I say that you haven't."   
"I always knew these pants made my ass look great." You murmured mostly to yourself.   
He tapped his finger against the table and made some remark about egotism that you didn't pay attention to because the ring around his finger was blinking in the light and -holy shit, he was married.

Your reaction was instant; you pushed your chair back and leaned away from the man you'd thought so highly of just a few moments ago.   
"You're married." You bit out aggressively, cutting him off and prompting a genuinely surprised expression which would have delighted you otherwise.   
"Yes, I-"   
"I don't date married men." You said coldly before standing and marching out of the fancy restaurant without another word. 

You felt embarassed and angry, your cheeks burned against the cold night air as you slowed on the sidewalk.   
He'd always worn those gloves, you'd never seen the ring and he'd never mentioned having a partner. You ran your hand through your hair and tugged as you thought over everything. Surely you would have remembered him saying something about being married.   
A hand pulling at your own snapped you out of your musings. You looked at the owner and scowled.   
"Kevin, I'm not-"   
"I'm in a permissive marriage. As long as Raymond knows what I'm doing and agrees with who I'm with it's fine."   
That took most of the anger out of your sails and left you with your mouth open.   
"I still don't like going into a relationship without knowing something so important." You grouched and thought about pulling your hand away, except Kevin had never touched you besides a handshake and his hand was warm and he was actually almost pleading as he looked at you.   
"Please understand that I made no effort to hide my marriage, I never intended to become interested in you and so I never saw the need to tell you." He was becoming more composed by the word, settling back into his normal self.   
"I do understand that. I just... I feel like an idiot. I mean, you just seem so much more... Upperclass than I am and now you're married and I-"   
"Be quiet."   
"What-"   
"Be. Quiet." Kevin instructed. "You're belittling yourself over a miscommunication. I wouldn't be interested in someone who could not match me." The timbre to his voice lowered towards his last statement and his hand tightened once before he let go.   
He straightened his blazer and squared his shoulders. "In conclusion, will you be rejoining me for our date?" 

You took a moment to wrestle internally with your thoughts.   
He was married, but there was an allowance and you really liked him. And it seems he really liked you.   
Wow, that was a short debate. 

"Yes, although I think we lost our table." You replied and nodded at the table that was now occupied by a family of three. "But I think I know a place we can go."   
The two of you started walking to the car, arms brushing occasionally.   
"There's this little book cafe nearby the college that stays open late and serves the best quiches."   
"I'm afraid I'm not quite dressed for it."   
"That's alright," you smiled "we'll be even then."


	4. What it's like to date them

Jake   
At first you two struggle to find balance. Between both of your demanding jobs on the force and your personal lives you have a hard time balancing your own lives, and then you add another one on top of that? It takes time to adjust.   
Once you do find that balance dating Jake is easy, and ridiculously fun.   
He's always pushing and supporting you to be the best and in turn you do the same. You're both secretly delighted by the fact that you have someone you can bounce thoughts off of when it comes to cases and sometimes you help each other solve the case. 

You're very competitive people, especially when competing against each other and that has driven many a stupid escapade. 

No matter how goofy the detective is, you know he'll always do his best by you. There's a fierce loyalty and protectiveness underneath all of his jokes that makes you feel more sure of yourself in times of doubt.   
Dating Jake sure is like finding your best friend except you get to bang. 

Amy   
Dating Amy is far more self-growth than you expected it to be.   
Once your relationship is official you're introduced to a myriad of hobbies and things you'd never heard about. After a month of dating you find you now have a schedule, all of your belongings are in some sort of order (usually alphabetic, by date or importance). It's rather frightening actually, how efficient you become once your girlfriend organises your chaos as you create it.   
On the flipside you teach her that some things don't need to categorised, she can enjoy life without needing to quantify it. 

Working around both of your busy schedules takes effort, between her being a workaholic with already long hours and you being an up and coming artist, you've got to make time for each other at odd hours. It isn't uncommon for you to join her at her desk for lunch or to crash in the breakroom when she's working nights so that you can spend some time together. It definitely puts strain on the relationship but you both try your best. 

Rosa  
It takes consistent kindness to break down the razor sharp outer walls that she keeps up. And behind those walls are slightly smaller walls. 

But still, you don't need her to say that she loves you and you don't need to say you love her. The fact that she puts the flowers you give her in her jacket pocket and is willing to fight anyone for you is enough.   
It helps that whenever you're spending the night together she's too sleepy to keep up her usual levels of aloofness and is happy to curl up next to you.   
Fun fact; she likes to be the little spoon but tell anyone that and she will arrest you. 

Holt  
It takes a while to get to a place where you can say that you're actually romantically together. After so many visits to the safehouse the two of you become rather close and once the threat to your life is over and you're finally free to live your life you find that you want Raymond to be in it.   
You're obviously introduced to Kevin at some point and he immediately picks up on the feelings you harbour for each other. He makes it his mission to get the two of you to admit it to each other.   
It takes a few weeks of scheming and prodding on Kevin's part before Raymond finally tells you, quite directly, that he's romantically interested in you.   
Kevin is almost unbearably smug about his part in getting the two of you together, but you think he's earned it after putting up with his husbnd's pining and your awkward attempts to hide your attraction. 

Dating Raymond involves calling him instead of 911 when something happens because he'll be unbearable and cause war between the 99th and other precincts if any of them happen to respond to your call before the 99 does. It's both a matter of pride and protectiveness, he only trusts his people to keep you safe.  
Be prepared for dates to be both fun and educational, and planned to a tee.   
He can and will give you a file of date ideas that are appealing and appropriate for your relationship.   
And yes, you can get him to do anything that's not on the list by presenting him with the thing you'd like to do and then dragging him along to it. If you have to endure a four hour barrel tour, he can accompany you to the arts and music festival.

Kevin  
Dating Kevin involves a lot of arguing about literature and pointless things. Many a date has been derailed by spirited discussions about the origin of corn dogs or the true motivations of the Friar from Romeo and Juliet.   
You need to be prepared to bicker whether you're waiting at the Opera or watching Die Hard at home under the condition that his viewing choice stays between the two of you. 

No matter how much he snarks and pokes, you know he's always willing to help. When you'd left your marking to the last minute for an art history class and bemoaned your poor planning skills he'd shown up at your door at 10 at night, armed with his campus satchel and the awful Chinese takeout he knew you liked.   
He'd never looked as handsome as he did that night, with his red pen poised critically over a student's paper while his other hand held half a spring roll.   
You know that in a week he'll complain to you about his students and you'll arrive at his office with tea and lunch, and you'll patiently listen to him rant about them splitting infinitives and butchering the English language. You'll even agree with him.


End file.
